Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents

Abstract

Free-radical-scavenging capacity antioxidant and membrane-protective properties of natural and related synthetic allylpolyalkoxybenzenes with different numbers of alkoxy/methoxy groups in the aromatic ring were evaluated using several in vitro models. These included the DPPH assay, inhibition of lipid peroxidation products accumulation, inhibition of H 2 O 2 -induced hemolysis, and oxidation of oxyhemoglobin. A synthetic protocol for the synthesis of natural nothoapiol (9) from a parsley seed metabolite, apiol (7), was developed. A structure−activity relationship study revealed that both the methylenedioxy fragment and methoxy groups in the aromatic ring are favorable for antioxidant activity. Hydroxyapiol ( 14), containing a hydroxy group in the aromatic core, was identified as the most potent compound. The pentaalkoxy-substituted nothoapiol (9) showed antioxidant activity in mouse brain homogenates, whereas in mouse erythrocytes it exhibited a marked pro-oxidant effect. Despite their low free-radical-scavenging capacity, allylpolyalkoxybenzenes can contribute to the total antioxidant potencies of plant essential oils.

Synthesis and Antioxidant Capacity of Some Derivatives of Sesamol at the C‐6 Position

“…It is known that this moiety can be actively metabolized both in vivo and in vitro , and the main metabolic pathway is its recyclization and demethylation to the catechol moiety [7,41] which confer antioxidant properties to the molecule. A high AOA in the same model was previously demonstrated for natural and synthetic allylpolyalkoxybenzenes containing a methylenedioxy moiety in the structure of the molecule, the DPPH‐test also showed their low RSA [36] …”

“…To assess the antioxidant potential of the synthesized compounds 2 – 5 , 7a – 12 , we used an already established set of methods [13,15–21,36,37] . Sesamol ( 1 ) and the standard antioxidant BHT (2,6‐di‐ tert ‐butyl‐4‐methylphenol) [38,39] were taken as the most suitable reference compounds.…”

“…MPA was determined by the degree of inhibition of H 2 O 2 ‐induced hemolysis, inhibition of the LPO secondary products accumulation. A detailed description of the experiments was presented in our previous works [13,15–18,36] …”

Correlation between total flavonoid content and total phenolic content on antioxidant activity of ethanol extracts from three cultivars of papaya leaves

“…Antioxidant components of plants play an important role, which may be effective as a therapeutic agent (Poojary et al, 2016). Plant extracts and essential oils are gaining increasing attention because natural antioxidants have little impact on human health and the environment, suitable for application in the pharmaceutical and food industry (Samet et al, 2019). Medicinal plants have many active substances such as lavonoids, tannins and polyphenols.…”

Reversal of Ovarian Cancer Cell Lines Multidrug Resistance Phenotype by the Association of Apiole with Chemotherapies

“…In mice tumor models [ 12 , 13 ], apiole promoted antitumor effects without clinical signs of toxicity up to 30 mg/kg, three times per week, by intraperitoneal route. In comparison to other allylbenzenes derivatives, apiole was found as the less potent genotoxic agent [ 30 , 31 ]. A careful toxicological study should be considered for apiole, once this molecule is popularly known by its abortive and toxic effects.…”